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Question

In which of the following pairs of compounds is the first molecule more reactive than the second molecule towards both SN1 and SN2?

A
II and IV
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B
I, II and III
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C
I, II, III and IV
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D
III only
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Solution

The correct option is B I, II and III

I) Rate of SN1 and SN2 for first molecule will be greater than the second. In SN1 reaction, the carbocation formed can be stabilized by the lone pair of oxygen by resonance. In SN2 reaction, oxygen increases the electrophilicity of the reactive site by inductive effect.


II) Rate of SN1 and SN2 for first molecule will be greater than the second. In SN1 reaction, the carbocation formed can be stabilized by the double bond by resonance. In SN2 reaction, sp2 carbon increases the electrophilicity of the reactive site by inductive effect.


III) Rate of SN1 and SN2 for the first molecule will be greater than the second. In SN1 reaction, the carbocation formed can be stabilized by resonace of benzene ring. In SN2 reaction, -R effect of benzene increases the electrophilicity of the reactive site. Also haloarenes are not reactive towards nucleophilic substitution.


IV) First molecule is more reactive towards SN1, since it is a tertiary substrate. The second molecule will be more reactive than the first one towards SN2 reaction.

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